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Cuckold Roleplay Fantasy

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Larry Takes Alyssa Shopping

Larry waited patiently as he  watched Alyssa disappear into the mall.  He never got tired of watching the sexy sway of her hips as she walked. He  followed her in a few minutes later, but was careful not to follow too close.  He knew she really wouldn’t want to be seen with him until it was time to for him to hand over money and hold her shopping bags. She never spent her money and Larry firmly believed she shouldn’t have to. It was really the only thing in their relationship he could actually  be proud of.  Alyssa was beautiful, confident and turned heads where ever she went. Any man would love to be her boyfriend. Even if Larry couldn’t satisfy her sexually with his small penis he more than made up for it by making sure she wanted for nothing.  After all it was the least he could do!

Alyssa Goes Out

Alyssa was out with her friends tonight. There was no telling when she would be back, if she came back tonight at all. He watched her do her hair and make up  and even helped her zip up the tight black lace dress she put on.  So he had the entire evening to himself. As much as he loved his wife, he had come to enjoy these times to himself.  He could taste the excitement the evening would bring. He took off of his clothes and carefully placed it on the hanger in the full walk-in closet, where the many shopping bags from the day were still stacked on top of each other waiting to be unpacked.

Cuckole Roleplay : What Happens Next

So.. am I really out with my friends? What is Larry going to do when he takes off his clothes? Guess what?! You get to decide what happens next in this cuckold roleplay fantasy! Send me an email, post on twitter, or give me a call and help me decide which way the story goes!

Cuckold Roleplay Fantasy


Six Days to Feminization: Day Four

Hello my lovely sissy students. Welcome to Day Four of my six day feminization series! I hope everyone had a wonderful Labor day weekend! I took a few days to hang out with friends and enjoy the last few days of summer! I know you’ve been eagerly waiting for the next step in my series of feminization. If you are just joining us make sure you catch by visiting Day OneDay Two and Day Three, of my six day erotic gender transformation guide.

Reflections on Feminization

Can you believe it?! We are halfway there and I am so proud of you all for making it this far! I’m  Now that we are halfway through my sissy transformation series and I’m so proud of you for making it this far!

I want you to take the time to reflect on what we’ve covered so far. I want you to take the time and really think about the last few exercises and think about how they’ve affected your way of thinking and everyday feminine habits. What do you feel like you can do better?

Sissy Check In

I want to hear from you! Time to check in and tell me how your sissy transformation journey has gone so far? You can leave a comment or send an email and let me know how you’re coming along with your sissy assignments and exercises.   You may have questions or want more personalized guidance on developing certain feminine habits don’t hesitate to set up a phone or sexy texting session with me!

feminization assignments


Six Day Guide to Feminization: Day 3

Hello girlies. Welcome to day three of my six part guide to feminization. I  know you all are very happy to be here! First I want to thank you for sharing your comments and following along! You are such good sissy students! If you are just joining us in our feminization transformation journey, make sure you  catch up with Day One and Day Two!

Using Your Imagination as a Guide to Feminization

Earlier this week we talked about how to visualizing yourself in panties is a great way to condition your mind to conform to feeling more feminine.  It’s been a couple of days and I hope you’ve all been practicing using your imagination to wearing pretty panties.

The Pussy Exercise

I want you to write visualize your pussy. What would it look like? Would you lips flare out like the petals of a flower or be a tightly closed little bud? If you had a pussy what would you call it? What would it smell like? How big would your clit be? Would it hang out a little or be tucked in? What color would your pubic hair be? Would you have a nice neat little busy or would you keep it smooth and bald? If you need some inspiration click here to view letter from a sissy of mine who completed this feminization assignment beautifully!

Tell Me about Your Pretty Pussy

I want to know what you look like down there! Now that you’ve thought about your pussy. Remember your pussy will be unique to you and like no one else.  It’s time to call me and describe it to me in vivid detail, or if you want I can help you discover what your hidden flower looks like!

Guide to Feminization

Six Days to Feminization: Day Two

Happy Monday! Here I am with the second installment to my Six Days to Feminization series. Day One can be found here! Remember small steps. Well day two of your feminization journey is learning how to wear panties all the time!

Putting on Panties

A lot my callers who desire to wear panties are unable to for many reasons. Some are unable to purchase them do to budget limitations or they may not have a discreet place to hide them from their wife or significant other. For others it make take a while to build up enough nerve to buy their first pair of pretty panties.

Using your Feminization Imagination

Wearing panties is a very big part of feminization and feeling feminine. But what if I told you that you didn’t have to actually wear panties to get the same results? How is this possible you ask? By visualizing and using your imagination. Using your imagination can help you expand your personal panty collection to limitless possibilities!

Picking Out Your Sissy Panties

I want you to pick out the panties you will wear for the next day. The best think about this is your inspiration can come from just about anywhere!  Check out different Mistresses at Sissy School and check out the panties they’re wearing. You can also browse through your lingerie sites, tumblr, or even the pair your wife put on today!


Now I want you to take the boxers you planned to wear today and visualize them melting into the pair of sexy lace thongs you saw your neighbor slip on through her bedroom window. Close your eyes as you put them on and imagine how good the delicate lace feels at is caresses your legs on the way up your body. Wiggle your hips a little as you pull them up over your bottom, and imagine how wicked that thong feels wedged between the soft cheeks of your girlie ass *giggle*

I Want to Put you in Panties

Visualizing can take a little practice but the more you do it the better you will become, not only at using your feminization imagination, but also conditioning your mind in all things girly! Want me to pick out your panties for you? I would LOVE to! Just give me a call and I will choose a pair of sissy panties especially for you!




Six Days to Feminization: Day One

Hello girly boys. So you feel you are ready to start your feminization  journey. This can sometimes be very overwhelming and you don’t know where to start! So I am going to be posting series of tips over the next 12 days to help you reach your goals. Did you know that even making small changes to your routine can make big impact on your feminization transformation.

Take Small Steps

So instead of trying to maybe big changes all at once, I’m going to give you six days of task I want you to incorporate into your daily routine. These feminization assignments help you get used to looking more feminine  and will also help to recondition your way of thinking over time to. Remember it’s not just about going through the motions and pretending you’re a girl. It’s about feeling that way on the inside and out!

This Week’s Feminization Task: Get your measurements

This week I want you to find a tape measure and learn how to measure your bust, waist and hips! Then I want you to write down your girly measurements and keep them in your wallet or smartphone or somewhere you can access the measurements when you are shopping for your first set of panties and bra! I know so exciting right! Lingerie sizes  vary greatly depending on brand and store. Your cute sissy girl figure may be a size 8 in one brand of panties and then be a size 12 in a different brand in the same store!

Need some guidance with this task?

I am always happy to help someone bring out the inner girl in them and I am just a call away if you need assistance with this feminization task.


feminization steps